Sodium Carbonate → HCID 22721628, compound

HRID 1581477Notes

Reaction equation

HRID 1581477 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[C:10](Br)=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:15][O:14][C:13]1[C:7]2[CH:6]=[C:5]([C:3]([OH:2])=[O:4])[S:9][C:8]=2[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 19007564HCID 19007564, compound

Product 1

HCID 22721628HCID 22721628, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-bromo-4-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (5 g, 16.6 mmol) with bis(triphenylphosphine)palladium (II) chloride (350 mg, 0.496 mmol, 0.03 eq.) and K2CO3 (4.88 g, 49.8 mmol, 3 eq.) under argon in dioxane (40 ml) at 20° C. was stirred for 60 minutes. Phenylboronic acid (2.16 g, 17.4 mmol, 1.05 eq.) and 2N Na2CO3 (80 ml) was then added and the mixture heated to 100° C. overnight. After cooling, filtration and acidification to pH 1 with aq. HCl the product precipitated and was filtered off and dried under vacuum at 50° C. to afford the title compound (3.16 g, 67% yield) as a light brown solid. MS m/z=282.9 (M−H).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration and acidification to pH 1 with aq. HCl the product
  3. customprecipitated
  4. filtrationwas filtered off
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-6241b40a182d4d24ba8982e30fc2da75
Source dataset
uspto-grants-2004_05
Patent number
US06730670B2

Reaction notes

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